Where to Find Some of Chicagoland's Most Picturesque Streets - bairdwarner.com
Where to Find Some of Chicagoland’s Most Picturesque Streets

Chicago is recognized the world over for its unique and diverse architecture. From the city to the suburbs, you can live in this area for your entire life and still find something marvelous, impressive, and new to discover every day — including some of the most scenic and picturesque streets you’ll find anywhere in the world. 

Looking for a new perspective? Whether you’re exploring Chicagoland on foot, by bike, or by car, here are seven stunning streets that showcase the best of Chicagoland’s culture and architecture. Don’t forget to bring your camera!

The B_Line: Hubbard Street Between River West and Fulton River District

If you’re fond of art, you’ll find this street to be one of the most picturesque and memorable in Chicago.

Sometimes known as the B_line, this strip of Hubbard street was started by Chicago native Ricardo Alonzo to give a home to what he saw as “a rebirth of social issues that had taken to the streets in the form of public art.” The murals that line this stretch of the city, painted and maintained by Illinois artists, depict everything from the area’s local wildlife to some of the unique cultural institutions with roots in Chicago. Both individual artists and larger organizations can donate a mural, so they change regularly. 

Hubbard Street is a great place to take photos — just make sure to tag the artists if you post them on social media. You can get more information about the project and its history, or even volunteer to help maintain the murals, at hubbardstreetmurals.com

Galena’s Main Street

Galena is a wonderful and picturesque community, whether you call it home or only plan to pop by for the weekend. While it’s a bit of a drive from Chicago itself, this quaint city is a favorite of history lovers. In fact, more than 85 percent of the town falls within a National Register Historic District, which includes more than 800 stunning buildings

Galena has been called one of the most beautiful tourist destinations in Illinois, and for good reason. Galena’s Main Street is lined with beautiful 19th Century-style architecture; when you head down the street you can almost imagine that you’re stepping back in time. Some of America’s most prominent historical figures either lived, worked, or stayed in Galena for periods of time. Abraham Lincoln gave speeches from the balcony of the DeSoto House Hotel, and General Ulysses S Grant’s family lived and worked in this celebrated spot. Looking for a scare? This area has also been called one of the most haunted destinations in Illinois.

Martin Luther King Drive in Bronzeville

Chicago’s Bronzeville neighborhood is a legendary home for music, business, art, and culture. Bronzeville became a hub for Black-funded and Black-owned businesses in Chicago in the 1920s, earning it the nickname “The Black Metropolis.” 

This area stretches out between a few streets that are easily walkable in order to take in all of the historic monuments and architecture, with South Martin Luther King Drive serving as the main thoroughfare.

For a perfect tour, Choose Chicago spotlights nine buildings that showcase the historical importance and cultural significance of Bronzeville, including the Overton Hygienic Building, a classic Chicago brick building. Nearby is the Chicago Bee Building on South State Street, a gorgeous Art Deco-style building that used to be home to the Bee newspaper. Not far from there is Unity Hall, located on South Indiana Avenue, another beautiful, classic red brick building that became home to the Peoples Movement Club in the 1920s. 

Michigan Avenue, from Oak Street to the River

There is a reason this stretch of Michigan Avenue in Chicago is called the Magnificent Mile. The rich diversity and history of Chicago’s architecture and art are easy to see in this part of the city, which features iconic architecture and sites including 875 North Michigan Avenue, the Tribune Tower, the NBC Tower, and the Historic Water Tower, which survived the Great Chicago Fire in 1871. Just a bit south, you’ll find some of the region’s most treasured public art, including the public sculpture Cloud Gate — more commonly and lovingly known as The Bean. 

Mag Mile also offers easy access to the Chicago Riverwalk, a gorgeous and relaxing oasis in the heart of the city, and puts you in close proximity to the Astor Street District in the Gold Coast, a cluster of historic architecture named for John Jacob Astor, who once held the title of wealthiest man in America. 

Oak Park’s Forest Avenue and N. Kenilworth Avenue

Oak Park is famous as the home to Frank Lloyd Wright, one of the most celebrated architects of all time. The famed architect designed 25 homes in this Chicago suburb, which is accessible from the city via a short ride on the “L.” 

Forest Avenue between Chicago Avenue and Lake Street offers views of six of those homes, designed in Wright’s distinct style. The architect’s desire to merge nature and architecture is apparent, as Forest Avenue is lined with tall, old trees that complete the gorgeous view. 

It’s not the only street in Oak Park where you can get a spectacular view of history. Just east is North Kenilworth Avenue, equally picturesque and worthy of a visit. There you’ll find two more homes designed by Frank Lloyd Wright, as well as the boyhood home of Ernest Hemingway. The entire Oak Park area is charming and scenic, with lots of trees and parks to enjoy on a spring or fall day. 

Chicago’s Alta Vista Terrace District

Stumbling upon the Alta Vista Terrace District feels like entering a dream. Situated just a stone’s throw from the heart of Wrigleyville, this quaint street feels like it got dropped in from the middle of London, with tiny row houses in a variety of classical styles all lined up along a narrow street. 

As Choose Chicago explains, this stunning stretch was the brainchild of developer Samuel Eberly Gross and architect Joseph C. Brompton. Sometimes known as “A Street of Forty Doors,” Alta Vista Terrace was designated as a historic district in 1971.

The Ridge Historic District in Beverly/Morgan Park

Located on the southern end of Chicago, Beverly is a charming and historic neighborhood — and home to one of the largest urban districts on the National Register of Historic Places. Designated in 1976, the Ridge Historic District runs from roughly W. 87 Street to W. 115 Street and features more than 3000 buildings. 

The area is also home to the nearby Beverly/Morgan Park Railroad Station District the Longwood Drive District, and the Walter Burley Griffin Place District, which collectively encompass a historic railroad station, a stunning castle, and impressive homes designed by noted architects like Frank Lloyd Wright, George W. Maher, Walter Burley Griffin, and Daniel Burnham.

Want to Keep Exploring?

Want to find more picturesque streets near you in Chicagoland? Your local Baird & Warner agent can help you find more fun things to see and do all over our area. 

Ready to make a move? Curious about how to start your search for the perfect home? Baird & Warner has called Chicagoland home since 1855. Whatever your real estate goals may be, we get you — and we’re here to help make things easier, at every step of the way.